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Iodoethane → 4-[3-[6-(3-Bromo-5-ethoxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

HRID 416976
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HRID 416976 반응식
[CH2:1]([O:3][C:4](=[O:38])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([CH2:28][OH:29])[CH:25]=[C:24]([Br:30])[CH:23]=2)[C:10]=1[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH3:2].I[CH2:40][CH3:41].[H-].[Na+]>CN(C)C=O.O.[Cl-].[Na+].O>[CH2:1]([O:3][C:4](=[O:38])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([CH2:28][O:29][CH2:40][CH3:41])[CH:25]=[C:24]([Br:30])[CH:23]=2)[C:10]=1[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 594968024-[3-[6-(3-Bromo-5-hydroxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

생성물 1

HCID 594967954-[3-[6-(3-Bromo-5-ethoxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester수율 53%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 4-[3-[6-(3-bromo-5-hydroxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (1.0 g, 1.68 mmol) in N,N-dimethylformamide (10 mL) was added iodoethane (403 μL, 5.04 mmol) and sodium hydride, 60% dispersion in mineral oil (202 mg. 5.04 mmol) at room temperature. The resulting suspension was stirred for 5 h. Then, the reaction mixture was diluted with water and brine. The organic compound was extracted into ethyl acetate and the combined organic extracts were washed with brine solution. The organic layers were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude material was purified by column chromatography (Isco™ 40 g) with 0-30% ethyl acetate/hexanes as eluting solvents to afford the title compound (550 mg, 53%) as a colorless oil.

후처리

  1. extractionThe organic compound was extracted into ethyl acetate
  2. washthe combined organic extracts were washed with brine solution
  3. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe crude material was purified by column chromatography (Isco™ 40 g) with 0-30% ethyl acetate/hexanes
  6. washas eluting solvents

출처 및 근거

ORD 기록
ord-11d984fe36024fcbb89d7c431bc264c6
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08088936B2

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